Sodium Bicarbonate → tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylate

HRID 491218

Reaktionsgleichung

Reaktionsgleichung von HRID 491218
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.[C:16](=O)([O:22]C(C)(C)C)[O:17][C:18]([CH3:21])([CH3:20])[CH3:19].C([O-])(O)=O.[Na+]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:22])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1

Komponenten

6

Edukt 3

HCID 516892Sodium BicarbonateHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 159258174-(4-Nitrophenyl)piperidine

Produkt 1

HCID 21940085tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylateAusbeute 83,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-(4-nitrophenyl)piperidine (412 mg, 2 mmol) in CH2Cl2 (100 mL) was added di-tert-butyl carbonate (480 mg, 2.2 mmol) and N,N-dimethylpyridin-4-amine (50 mg, 0.4 mmol). The mixture was stirred for 20 h at room temperature. The mixture was added saturated NaHCO3 (100 mL). The organic layer was separated and aqueous was extracted with CH2Cl2 (50 mL×2). The combined organic solution was dried and concentrated in vacuo. The residue was dissolved in MeOH and bubbled with Ar for 2 min. before adding 10% Pd—C. The hydrogenation was finished in 4 h. The catalyst was removed by filtration and solvent was removed in vacuo to afford title compound (460 mg, 83%) as white solid.

Aufarbeitung

  1. customThe organic layer was separated
  2. extractionaqueous was extracted with CH2Cl2 (50 mL×2)
  3. customThe combined organic solution was dried
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in MeOH
  6. custombubbled with Ar for 2 min.
  7. additionbefore adding 10% Pd—C
  8. waitThe hydrogenation was finished in 4 h
  9. customThe catalyst was removed by filtration and solvent
  10. customwas removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-85d34c0e64314517801fff44d77b368f
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528143B2

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